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Synthesis 2015; 47(14): 2017-2031
DOI: 10.1055/s-0034-1380868
DOI: 10.1055/s-0034-1380868
feature
Catalysis Inside Dendrimers
Further Information
Publication History
Received: 17 March 2015
Accepted after revision: 02 May 2015
Publication Date:
22 June 2015 (online)
Abstract
Modern methods that involve intradendritic catalysis are introduced in this feature article. Supramolecular principles, therefore, derive from the concept of the unimolecular dendritic micelle introduced by Newkome. When the micellar effect is combined with intradendritic ligand acceleration, copper(I) catalysts or palladium nanoparticles (PdNPs) are required at the ppm level for efficient reactions. Applications range from organic catalysis to catalysis by metal complexes of intradendritic ligands and dendrimer-stabilized nanoparticles (NPs) that are located at the dendrimer core or between the dendrimer tethers. Bimetallic nanoparticle-cored dendrimers including superparamagnetic iron oxide nanoparticles (SPIONs) are especially promising due to very facile magnetic separation.
1 Introduction
2 Supramolecular and Organic Catalysis inside Dendrimers
3 Micellar Dendritic Catalysis: Olefin Metathesis and Click Reactions
3.1 Olefin Metathesis
3.2 Click Chemistry
4 Combined Micellar Dendritic Effect and Intradendritic Ligand Acceleration
5 Efficient Click Catalysis at the Dendrimer Core
6 Dendrimer-Encapsulated and Dendrimer-Stabilized Nanoparticle Catalysts
7 Catalysis by Nanoparticle-Cored Dendrimers
8 Concluding Remarks
-
References
- 1 Modern Surface Organometallic Chemistry. Basset J.-M, Psaro R, Roberto D, Ugo R. Wiley-VCH; Weinheim: 2009
- 2 Handbook of Heterogeneous Catalysis. Ertl G, Knözinger H, Schüth F, Weitkamp J. Wiley-VCH; Weinheim: 2008
- 3 Somorjai GA, Li Y. Introduction to Surface Chemistry and Catalysis. 2nd ed. Wiley; New York: 2010
- 4 Basset JM, Coperet C, Soulivong D, Taoufik M, Cazat JT. Acc. Chem. Res. 2010; 43: 323
- 5 Crooks RM, Zhao M, Sun L, Chechik V, Yeung LK. Acc. Chem. Res. 2001; 34: 181
- 6 Phan NT. S, van der Sluys M, Jones CW. Adv. Synth. Catal. 2006; 348: 609
- 7 Ferrando R, Jellinek J, Johnston RL. Chem. Rev. 2008; 108: 845
- 8 Lu A.-H, Salabas EL, Schüth F. Angew. Chem. Int. Ed. 2007; 46: 1222
- 9 Lou XW, Archer LA, Yang Z. Adv. Mater. (Weinheim, Ger.) 2008; 20: 3987
- 10 Shylesh S, Schünemann V, Thiel WR. Angew. Chem. Int. Ed. 2010; 49: 3428
- 11 Polshettiwar V, Luque R, Fihri A, Zhu H, Bouhrara M, Basset J.-M. Chem. Rev. 2011; 111: 3036
- 12 Gawande MB, Branco PS, Varma RS. Chem. Soc. Rev. 2013; 42: 3371
- 13 Astruc D, Lu F, Ruiz J. Angew. Chem. Int. Ed. 2005; 44: 7852
- 14 Welton T. Coord. Chem. Rev. 2004; 248: 2459
- 15 Zaera F. Chem. Soc. Rev. 2013; 42: 2746
- 16 Toshima N, Yonezawa T. New J. Chem. 1998; 22: 1179
- 17 Riess G. Prog. Polym. Chem. 2003; 28: 1107
- 18 Newkome GR, He E, Moorefield CN. Chem. Rev. 1999; 99: 1689
- 19 van Heerbeek R, Kamer PC. J, van Leeuwen PW. N. M, Reek JN. H. Chem. Rev. 2002; 102: 3717
- 20 Dendrimer Catalysis. In Topics in Organometallic Chemistry. Vol. 20. Gade LH. Springer; Heidelberg: 2006
- 21 Reek JN. H, Arévalo S, van Heerbeek R, Kamer PC. J, van Leeuwen PW. N. M. Adv. Catal. 2006; 49: 71
- 22 Andrés R, de Jesús E, Flores JC. New J. Chem. 2007; 31: 1161
- 23 Hwang S.-H, Shreiner CD, Moorefield CN, Newkome GR. New J. Chem. 2007; 31: 1192
- 24 de Jesús E, Flores JC. Ind. Eng. Chem. Res. 2008; 47: 7968
- 25 Myers VS, Weir MG, Carino EV, Yancey DF, Pande S, Crooks RM. Chem. Sci. 2011; 2: 1632
- 26 Astruc D, Chardac F. Chem. Rev. 2001; 101: 2991
- 27 Wang D, Astruc D. Coord. Chem. Rev. 2013; 257: 2317
- 28 Lee J, Farha OK, Roberts J, Scheidt KA, Nguyen ST, Hupp JT. Chem. Soc. Rev. 2009; 38: 1450
- 29 Ma L, Abney C, Lin W. Chem. Soc. Rev. 2009; 38: 1248
- 30 Furukawa H, Cordova KE, O’Keefe M, Yaghi OM. Science (Washington, D.C.) 2013; 341: 974
- 31 Gascon J, Corma A, Kapteijn F, Llabrés i Xamena FX. ACS Catal. 2014; 4: 361
- 32 Lu ZL, Lindner E, Mayer HA. Chem. Rev. 2002; 102: 3543
- 33 Moreno-Castilla C, Maldonaso-Hódar FJ. Carbon 2005; 455
- 34 Sanchez C, Julian B, Belleville P, Popall M. J. Mater. Chem. 2005; 15: 3559
- 35 Debecker DP, Mutin PH. Chem. Soc. Rev. 2012; 41: 3624
- 36 Kango S, Kalia S, Celli A, Njuguna J, Habibi Y, Kumar R. Prog. Inorg. Sci. 2013; 38: 1232
- 37 Scharze M, Pogrzeba T, Volovych I, Schomäcker R. Catal. Sci. Technol. 2015; 5: 24
- 38 Dalko PI, Moisan L. Angew. Chem. Int. Ed. 2004; 43: 5138
- 39 Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745
- 40 El Kadib A. ChemSusChem 2015; 8: 217
- 41 Dupont J, de Souza RF, Suarez PA. Z. Chem. Rev. 2002; 102: 3667
- 42 Ionic liquids: Armand M, Endres F, MacFarlane DR, Ohno H, Scrosati B. Nat. Mater. 2009; 8: 621
- 43 Sheldon R. Green Chem. 2014; 16: 950
- 44 Fu Q, Wagner T. Surf. Sci. Rep. 2007; 62: 431
- 45 Zhao Y, Jiang L. Adv. Mater. (Weinheim, Ger.) 2009; 21: 3621
- 46 Huang X, Tang S, Mu X, Dai Y, Chen GX, Zhou ZY, Ruan F, Yang Z, Zheng N. Nat. Nanotechnol. 2011; 6: 28
- 47 Newkome GR, Moorefield CN, Vögtle F. Dendrimers and Dendrons. Concepts, Syntheses, Applications. Wiley-VCH; Weinheim: 2001
- 48 Astruc D, Boisselier E, Ornelas C. Chem. Rev. 2010; 110: 1857
- 49 Gross E, Somorjai GA. Top. Catal. 2014; 57: 812
- 50 Brunner H. J. Organomet. Chem. 1994; 500: 39
- 51 Fan Q.-H, Li Y.-M, Chan AS. C. Chem. Rev. 2002; 102: 3385
- 52 Kassube JK, Gade LH. Top. Organomet. Chem. 2006; 20: 61
- 53 Helms B, Fréchet JM. J. Adv. Synth. Catal. 2006; 348: 1125
- 54 Klein Gebbink RJ. M, Virboul MA. N In Enantioselective Homogeneous Supported Catalysis. Šebesta R. Royal Society of Chemistry; Cambridge: 2012. Chap. 5
- 55 John A, Nachtigall FN, Santos LS. Curr. Org. Chem.. 2012; 16: 1776
- 56 Caminade A.-M, Turrin C.-O, Laurent R, Ouali A, Delavaux-Nicot B. Dendrimers. Wiley; Chichester: 2011
- 57 He Y.-M, Feng Y, Fan Q.-H. Acc. Chem. Res. 2014; 47: 2894
- 58 Bhyrappa P, Young JK, Moore JS, Suslick KS. J. Mol. Catal. A: Chem. 1996; 113: 109
- 59 Zhao M, Crooks RM. Angew. Chem. Int. Ed. 1999; 38: 364
- 60 Liang CO, Helms B, Hawker CJ, Fréchet JM. Chem. Commun. 2003; 2524
- 61 Caminade A.-M, Ouali A, Keller M, Majoral J.-P. Chem. Soc. Rev. 2012; 41: 4113
- 62 Imada Y, Kugimiya Y, Iwata S, Komiya N, Naota T. Tetrahedron 2013; 69: 8572
- 63 Maeno Z, Mitsudome T, Mizugaki T, Jitsukawa K, Kaneda K. Chem. Lett. 2012; 41: 801
- 64 Zhang F, Li Y, Li Z.-W, He Y.-M, Zhu S.-F, Fan Q.-H, Zhou Q.-L. Chem. Commun. 2008; 6048
- 65 Ma B, Miao T, Sun Y, He Y, Liu J, Feng Y, Chen H, Fan Q.-H. Chem. Eur. J. 2014; 20: 9969
- 66 Ding Z.-Y, Chen F, Qin J, He Y.-M, Fan Q.-H. Angew. Chem. Int. Ed. 2012; 51: 5706
- 67 Ma B, Ding Z, Liu J, He Y, Fan Q.-H. Chem. Asian J. 2013; 8: 1101
- 68 Liu J, Ma B, Feng Y, He Y, Fan QH. Inorg. Chim. Acta 2014; 409: 156
- 69 Newkome GR, Yao Z, Baker GR, Gupta VK. J. Org. Chem. 1985; 50: 2003
- 70a Newkome GR, Moorefield CN, Baker GR, Saunders MJ, Grossman SH. Angew. Chem., Int. Ed. Engl. 1991; 30: 1178
- 70b Newkome GR, Moorefield CN. US 5,154,853, 1992
- 71 Bosman AW, Janssen HM, Meijer EW. Chem. Rev. 1999; 99: 1665
- 72 Lee CC, MacKay JA, Fréchet JM. J, Szoka FC. Nat. Biotechnol. 2005; 23: 1517
- 73 Deraedt C, d’Halluin M, Astruc D. Eur. J. Inorg. Chem. 2013; 4881
- 74 Olefin Metathesis. Theory and Practice. Grela K. Wiley; Hoboken: 2014: 5
- 75 Davis KJ, Sinou D. J. Mol. Catal. A: Chem. 2002; 177: 173
- 76 Polshettiwar V, Varma RS. J. Org. Chem. 2008; 73: 7417
- 77 Gułajski L, Śledź P, Lupa A, Grela K. Green Chem. 2008; 10: 271
- 78 Diallo AK, Boisselier E, Liang L, Ruiz J, Astruc D. Chem. Eur. J. 2010; 16: 11832
- 79 Pijnenburg NJ. M, Tomás-Medivil E, Mayland KE, Kleijn H, Lutz M, Spek AL, van Koten G, Klein Gebbink RJ. M. Inorg. Chim. Acta 2014; 409A: 163
- 80 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 81 Tornøe CW, Christensen C, Meldal M. J. Org. Chem. 2002; 67: 3057
- 82 Meldal M, Tornøe CW. Chem. Rev. 2008; 108: 2952
- 83 Hein JE, Fokin VV. Chem. Soc. Rev. 2010; 39: 1302
- 84 Liang L, Ruiz J, Astruc D. Adv. Synth. Catal. 2011; 353: 3434
- 85 Golas PL, Tsarevsky NV, Sumerlin BS, Matyjaszewski K. Macromolecules 2006; 39: 6451
- 86 Golas PL, Tsarevsky NV. S, Matyjaszewski K. Macromol. Rapid Commun. 2008; 29: 1167
- 87 Zhao P, Grillaud M, Salmon L, Ruiz J, Astruc D. Adv. Synth. Catal. 2012; 354: 1001
- 88 Astruc D, Liang L, Rapakousiou A, Ruiz J. Acc. Chem. Res. 2012; 45: 630
- 89 Deraedt C, Pinaud N, Astruc D. J. Am. Chem. Soc. 2014; 136: 12092
- 90a Ornelas C, Ruiz J, Cloutet E, Alves S, Astruc D. Angew. Chem. Int. Ed. 2007; 46: 872
- 90b Ornelas C, Salmon L, Ruiz J, Astruc D. Chem. Commun. 2007; 4946
- 90c Franc G, Kakkar A. Chem. Commun. 2008; 5267
- 91 Ornelas C, Salmon L, Ruiz J, Astruc D. Chem. Eur. J. 2008; 14: 50
- 92 Boisselier E, Salmon L, Ruiz J, Astruc D. Chem. Commun. 2008; 5788
- 93 François A, Laroche A, Pinaud N, Salmon L, Ruiz J, Robert J, Astruc D. ChemMedChem 2011; 6: 2003
- 94 Breslow R In Advances in Enzymology and Related Areas of Molecular Biology. Vol. 58. Meister A. John Wiley & Sons; New York: 1986: 1-60
- 95 Rapino LD, Nord FF. J. Am. Chem. Soc. 1941; 63: 2745
- 96 Daniel M.-C, Astruc D. Chem. Rev. 2004; 104: 293
- 97 Scott RW. J, Wilson OM, Crooks RM. J. Phys. Chem. B 2005; 109: 692
- 98 Diallo AK, Ornelas C, Salmon L, Ruiz J, Astruc D. Angew. Chem. Int. Ed. 2007; 46: 8644
- 99 Astruc D. Tetrahedron: Asymmetry 2010; 21: 1041
- 100 Djeda R, Rapakousiou A, Liang L, Guidolin N, Ruiz J, Astruc D. Angew. Chem. Int. Ed. 2010; 49: 8152
- 101 Ornelas C, Ruiz J, Salmon L, Astruc D. Adv. Synth. Catal. 2008; 350: 837
- 102 Deraedt C, Salmon L, Etienne L, Ruiz J, Astruc D. Chem. Commun. 2013; 49: 8169
- 103 Astruc D. Nat. Chem. 2012; 4: 255
- 104 Deraedt C, Salmon L, Astruc D. Adv. Synth. Catal. 2014; 356: 2525
- 105 Deraedt C, Astruc D. Acc. Chem. Res. 2014; 47: 494
- 106 Gatard S, Liang L, Salmon L, Ruiz J, Astruc D, Bouquillon S. Tetrahedron Lett. 2011; 52: 1842
- 107 Boisselier E, Diallo AK, Salmon L, Ornelas C, Ruiz J, Astruc D. J. Am. Chem. Soc. 2010; 132: 2729
- 108 Zhao P, Li N, Salmon L, Liu N, Ruiz J, Astruc D. Chem. Commun. 2013; 49: 3218
- 109 Li N, Zhao P, Salmon L, Ruiz J, Zabawa M, Hosmane NS, Astruc D. Inorg. Chem. 2013; 52: 11146
- 110 Wang Y, Salmon L, Ruiz J, Astruc D. Nat. Commun. 2014; 5: 3489
- 111 Li N, Echeverria M, Moya S, Ruiz J, Astruc D. Inorg. Chem. 2014; 53: 6954
- 112 Li N, Zhao P, Liu N, Echeverria M, Moya S, Salmon L, Ruiz J, Astruc D. Chem. Eur. J. 2014; 20: 8363
- 113 Ciganda R, Li N, Deraedt C, Gatard S, Zhao P, Salmon L, Hernández R, Ruiz J, Astruc D. Chem. Commun. 2014; 50: 10126
- 114 Zhao P, Feng X, Huang D, Yang G, Astruc D. Coord. Chem. Rev. 2015; 287: 114
- 115 Daniel M.-C, Ruiz J, Nlate S, Palumbo J, Blais J.-C, Astruc D. Chem. Commun. 2001; 2000
- 116 Labande A, Ruiz J, Astruc D. J. Am. Chem. Soc. 2002; 124: 1782
- 117 Daniel M.-C, Ruiz J, Nlate S, Blais J.-C, Astruc D. J. Am. Chem. Soc. 2003; 125: 2617
- 118 Lu F, Ruiz J, Astruc D. Tetrahedron Lett. 2004; 45: 9443
- 119 Wunder S, Polzer F, Lu Y, Ballauff M. J. Phys. Chem. C 2010; 114: 8814
- 120 Wunder S, Lu Y, Albrecht M, Ballauff M. ACS Catal. 2011; 1: 908
- 121 Hervés P, Pérez-Lorenzo M, Liz-Marzán LM, Dzubiella J, Lu Y, Ballauff M. Chem. Soc. Rev. 2012; 41: 2467
- 122 Zhu Y, Stubbs LP, Ho F, Liu R, Ship CP, Maguire JA, Hosmane NS. ChemCatChem 2010; 2: 365
- 123 Rossi LM, Costa NJ. S, Silva FP, Wojcieszak R. Green Chem. 2014; 16: 2906
- 124 Kainz QM, Reiser O. Acc. Chem. Res. 2014; 47: 667
- 125 Yuzik-Klimova EY, Kuchkina NV, Sorokina SA, Morgan DG, Boris B, Nikoshvili LZ, Lyubinova NA, Matveeva VG, Sulman EM, Stein BD, Mahmoud WE, Al-Ghamdi AA, Kostoupoulou A, Lappas A, Shifrina ZB, Bronstein LM. RSC Adv. 2014; 4: 23271
- 126 Wang D, Astruc D. Chem. Rev. 2014; 114: 6949
- 127 Wang D, Deraedt C, Salmon L, Labrugère C, Etienne L, Ruiz J, Astruc D. Chem. Eur. J. 2015; 21: 1508
- 128 Deraedt C, Wang D, Salmon L, Etienne L, Labrugère C, Ruiz J, Astruc D. ChemCatChem 2015; 7: 303
- 129 Morgan DG, Boris BS, Kuchkina NV, Yuzik-Klimova EYu, Sorokina SA, Stein BD, Svergun DI, Spilotros A, Kostoupoulou A, Lappas A, Shifrina ZB, Bronstein LM. Langmuir 2014; 30: 8543
- 130 Bronstein LM. ChemCatChem. 2015; 7: 1058
- 131 Murugan E, Jebaranjitham JN. Chem. Eng. J. 2015; 259: 266